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Lisa has owned this dress and its matching jacket for nearly 20 years. She always wanted to be able to fit back into it, and now she can. "It's difficult to tailor a jacket, so get rid of those that are out-of-date," Adam says. A more contemporary covering is a chiffon bolero (Rickie Freeman Teri Jon, $145, TeriJon.net) or a shawl over the shoulders. Adam also modernized the dress by having it lengthened and pegged (that is, tapered inward as it comes down the leg). Bag, Kaia Peterka, $345; KaiaPeterka.com. Satin heels, Nina, $70; NinaShoes.com.
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